


Chastity's Bar

by JJ1564



Category: Supernatural
Genre: Barebacking, Bondage, Bottom Dean, M/M, Rimming, Transvestite
Language: English
Status: Completed
Published: 2014-04-11
Updated: 2014-04-11
Packaged: 2018-01-19 00:00:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,623
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1447831
Author URL: https://archiveofourown.org/users/JJ1564/pseuds/JJ1564
Summary: <blockquote class="userstuff">
              <p>Dean and Sam run into a familiar face in a bar called 'Chastity's'.  Dean gets to know the bar owner extremely well.</p>
            </blockquote>





	1. Part One

Dean and Sam dressed in their usual FBI suits and headed into ‘Chastity’s’ bar. Sam looked uncomfortable and Dean tried not to smile. He knew that Sam was not homophobic but being so tall, muscular and good looking made him a magnet for both men and women. Sam usually had no trouble dealing with women, but he was out of his comfort zone. Not Dean, however. Dean had been to numerous gay bars and was equally enjoyed flirting with and fucking with both sexes.

'So, shall we just ask the barman?' Sam said, his voice slightly higher than usual, betraying his nervousness. It was still early, barely 9pm and the bar was half empty. They drew everyone's attention, some looks were hostile as they were obviously police or FBI and some were openly admiring.

'Sure.' Dean nodded to Sam and slotted them into an empty gap along the bar. 'Excuse me dude, we need to ask a few questions.'

The barman was Latino and so camp he looked like he had modeled himself on Agador Spartacus from The Birdcage. 'Hello!' He eyed them both up and down and smiled. 'Anything for you. Either of you. Or both of you.'

Dean chuckled. 'Sorry sweetheart, business not pleasure. I'm Agent Deacon, this is Agent May.' They both flashed him their ID badges.

Agador pouted. 'Such a shame. How can I help?'

'Did you know Jeremy Flynn who worked here?' Sam said, his voice now sounding too deep, like he was trying to be more manly. Dean hid his smile again.

'Sure.' Agador's face grew serious. 'Jerry was a good guy. A bit too friendly though. I told him he'd get into trouble.'

 

'Friendly with the clientele?' Dean asked.

'Yeah. He couldn't resist a big guy, you know, tall, broad shouldered, just like you two. Especially you.' He gave Sam a long and wistful look.

'You think it was someone he hooked up with here?' Sam said, ignoring the look.

'Guess so. I wasn't on duty that night though, but Chas will know. The owner. He never misses a trick.' Agador pressed a button under the counter. 'He'll be down in two shakes.'

'Thanks.' Dean smiled at the barman. Then he felt Sam nudge him.

'Dean....' Sam's voice was weird.

Dean turned to see what had spooked his brother and he felt his chest tighten. He was not sure if it was from fear or another hidden emotion.

'Hendricksen?' He gasped in shock. 'No...it can't be.'

'What the hell are you doing here?' Sam said.

The vision walking towards them looked confused. He was almost as tall as Sam. probably taller in his high heels. He wore black fish net stockings and a tight vivid pink sequinned dress that reached his mid-thigh. He had a blonde wig and huge false eyelashes. He was clean shaven but otherwise he was a dead ringer for Agent Victor Hendrickson, an FBI agent who had hunted them down, captured them and then helped them fight off a host of demons several years ago, only to be killed by Lilith.

'Do I know you guys? I'm sure I'd remember such fine specimens of manhood!' He teased as he sashayed up to them.

Dean had never found transvestites appealing; he liked men for what they could do for him, things that women couldn't. But he had really liked Agent Hendrickson; he’d had many wet dreams about him and had felt miserable and guilty when he had been slaughtered. And now here he was, looking incredibly sexy and naughty. Dean could feel his dick hardening.

'Victor?' His voice came out little more than a squeak.

The vision laughed a deep throaty sound. 'Nope. Sorry honey my twin bro's no longer with us. I'm Charles Hendrickson. But you, pretty little Fed, can call me Chas.' Chas held his hand out to Dean and they shook hands, holding on far too long, Dean seemingly unable to speak or take his eyes off of the vision that was Charles Hendrickson.

'So you're Chas, as in Chastity?' Sam recovered his equilibrium faster than Dean. 'The owner?'

'That's me.' Chas was now shaking Sam's hand. 'And you are?'

'I'm Agent May, this is my partner Agent Deacon.' Sam said, shooting Dean a quizzical glance.

'They want to know about Jerry.' Agador butted in, grinning at Dean and giving him a wink. 'I think the little one likes you, Chastity.'

'What, no, I...' Dean stuttered as Chas laughed again. 'You just look so much like Victor. Kind of a shock.'

'Tell you what, Agent Pretty.' Chas said. 'You two come back into my office and you can tell me how you knew Victor and I'll tell you all I can about poor Jerry.'

Dean and Sam followed Chas through the bar and out the back.

'What the hell Dean?' Sam whispered. 'What's wrong with you?'

'Nothing.' Dean said sullenly.

'It wasn't your fault.' Sam said, misreading the source of Dean's discomfiture. 'We couldn't have known Lilith would show up.'

'Those people still died on my watch.' Dean hissed back, playing along with Sam. Of course he felt responsible for Victor’s death, he always felt responsible when anyone died on his watch, but Sam didn't need to know that was not the reason for his reaction this time.

Once inside his large and luxurious office, Chas invited them to sit down and poured three large whiskeys from a decanter.

'And don't bother with the no drinking on duty line. You both look like you need a stiff drink.' Chas said with a smile. 'So, tell me Agents Pretty and Stretch, how did you know my little brother?'

'We worked with him on a case.' Sam said, his voice edged with irritation at being called Stretch. 'And I thought you said you were twins? How was he your little brother?'

'We were twins, but I entered the world first and it always pissed Victor off.' Chas chuckled. 'We were never close, not like people think twins should be. We were too different. He hated the fact I liked to strip off all our action men and play with them naked. By the time we got to High School and he was into American football and I was into Hollywood musicals, we barely spoke.' Chas frowned now. 'I left home when I was fifteen, sick of my dad trying to beat the bad outta me. Only saw Victor once or twice a year after that. Different paths.'

'Very different.' Dean smiled. 'But you freaked me out a little, you're so alike.'

'Apart from the dress and the heels I guess!' Chas smiled back.

'So, about Jerry.' Sam intervened, throwing Dean another quizzical look. 'Do you know if he hooked up with anyone that night?'

'The night he was murdered? Yeah, sure, I told the police all I knew. Not that they did anything. A fag gets killed and they don't exactly pull out all the stops, y'know.' Chas sighed.

'We believe Jerry's death could be linked to a series of murders. We will pull out all the stops Mr Hendrickson.' Sam said sincerely. 'Please tell us all you know.'

Chas told them Jerry had been flirting with a tall, skinny guy all evening. The guy was thin but wiry, looked like he could take care of himself. He had dark hair and piercing blue eyes. Very pretty but he had looked cruel and Chas had told Jerry to be careful. Dean was not sure if it was the whiskey affecting him but he was mesmerized by Chas. He could have sat listening to him talk and watching his handsome face for hours.

'That sounds like our guy, doesn't it Agent Deacon?' Sam said. 'Agent Deacon!' He added louder.

'Um, sorry, yeah it does.' Dean tore his eyes from Chas, who gave him a knowing smirk and nodded to Sam.

'Is there anything else you can tell us Mr Hendrickson?' Sam said, ignoring Dean. 'Had you seen the man before, or since?'

'Nope, sorry. I tend to know all our regulars and I always remember pretty faces. I'd have remembered him for sure.'

'Well thank you, it's been most helpful.' Sam stood up, his whiskey untouched. He shook hands politely with Chas.

'My pleasure.' Chas said. 'Why don't you two hang around for a while? We have a great tribute act tonight, Lady Dada.'

'Sorry we're still on the clock.' Sam said. Dean stood up too and as he shook hands with Chas once more he felt his knees grow weak.

'If you need anything else, anything at all, you know where to find me.' Chas said, staring intently at Dean.

Dean licked his lips and nodded. 'Thanks, you've been real helpful.'

 

Dean felt like he was in a daze as he drove back to the motel. Sam tried to talk to him about the case but he gave up after a few grunted responses from Dean. All Dean could think about was that long body in that short pink dress, those big brown eyes, those full kissable lips and he knew he had to go back. Once back at the motel, Dean pretended to have left his cell behind. Sam rolled his eyes and cursed him, but opted to stay behind and do some research while Dean drove back to Chastity's, much to Dean's relief.

'Hi pretty little Agent.' Chas was by the door and almost seemed to be waiting for him. 'Come on upstairs.'

Dean nodded, speechless, and followed Chas, watching the way his firm buttocks swayed under the sequins and taking in his broad shoulders and long legs.

Chas unlocked a door and they stepped into a smart, well-furnished lounge. It was different to what Dean had expected, with a big black leather couch and chrome and glass furnishings. 'This is my apartment. The first door is my bedroom, but we're not going in there.' Chas moved so that he had Dean pressed up against the wall. Dean's heart was hammering and he suddenly felt very small and vulnerable. 'Ask me why not, Pretty.'

'Why...why not?' Dean managed to get out.

'I don't take one night stands into my bedroom. And I think I know what you need.' Chas winked.

'Fuck.' Dean gasped as Chas accompanied the wink by grabbing Dean's already hard dick through his thin trousers.

'Yeah. I told you I know what you need, my pretty little agent.' Chas bent down and kissed Dean roughly on the lips and Dean knew he probably had lipstick smeared all over his mouth now. And he didn’t care. 'You like it rough don't you?' Dean nodded, panting now. 'And I think you had a little thing for Victor, didn't you? Or is it all big black men?' Chas rubbed his groin against Dean's and it was obvious that Chas was indeed a very big man.

'Just...just Victor and...and you.' Dean gasped. Chas laughed and moved away, grabbing Dean's arm and propelling him along the hallway, stopping at a doorway.

'Welcome Pretty to my pink room of pain.' Chas said, opening the door with a flourish.

Dean's eyes widened when he saw the room. It was like an S&M dungeon decorated by Liberace. There was a St Andrew's cross with a pink painted wooden frame, a wall covered in whips, canes, Dildos, butt plugs, nipple clamps, all in various shades of pink and various sizes. There was a large bed covered in pink satin throws and pillows, with chains fitted at either end with pink fur lined wrist and ankle cuffs.

'Strip off Pretty and lie on the bed with your head up on the pillows.' Chas winked. 'For starters.' Dean moved like someone in a dream and was soon propped up naked on the pillows.

Chas stood watching him and once Dean was settled, he unzipped his dress and wriggled it down his body. 'If you were wondering Agent Pretty, I don't wear anything underneath except for my corset.' Chas said as he stepped out of the dress. He wore a tight black corset, which made his waist look tiny and his chest extra broad. But Dean's eyes had moved down and suddenly his mouth went dry. The corset ended at the hips showing off his massive erection. Chas was way bigger than anyone Dean had ever seen.

'Like what you see, Pretty?' Chas drawled and walked slowly over to the bed, his already hard dick swaying as he moved. Dean licked his lips and nodded.

'I've got so many plans for you but I really need to fuck you. Wanted that since I saw you. You wanted it too.' Chas climbed onto the bed and crawled up Dean's body. Dean was shaking in fear and arousal. 'Don't worry little pretty, I'll prep you good. Now arms up.'

Dean liked to be dominated and used, but he always struggled with any type of restraint. It was his hunter instinct he guessed that made him wary of being restrained and vulnerable. But he looked into Chas's big brown eyes and knew that he could trust him. Dean stretched his arms over his head and Chas fitted the cuffs around each wrist. Then he kissed Dean again, his big full lips so soft and inviting. Too soon he pulled away and chuckled at the sight of Dean, whose mouth was open and wanting more.

'Later my pretty. Now let's get down to business.' Chas kissed and licked his way down Dean's body, the long hair from his wig tickling Dean's skin and making him shiver even more. Chas then peppered kisses over Dean's erect dick as Dean's hips jerked and his body bucked up for more. Chas looked up. 'Fuck, everything about you is so fucking pretty. Bet your little hole is just as sweet as your dick.'

'Chas...please.' Dean begged. 'Need...'

Chas frowned and grabbed Dean's balls, squeezing them tight. Dean screamed and tried to kick Chas off, but he was kneeling over Dean's thighs and Dean was trapped. 'I know what you need. And I'll tell you when you can speak, okay?'

Dean nodded, tears in his eyes, and Chas released him. The pain had made Dean's erection waiver, which in some ways was a relief because Dean had ever been so turned on in his life.

'Good boy. Now let's get you ready.' He pushed Dean's legs up and apart, holding them while he stuck his head between them and rimmed his hole. Dean gasped and writhed, wanting more, needing more. Chas chuckled and the vibrations run over Dean's skin, making him shake more. Soon Chas's tongue was inside Dean, exploring his hole, swiping over his prostate again and again until Dean screamed as he came, embarrassingly fast and untouched, pumping his load over his own stomach.

Chas sat up, grinning and licking his lips. 'Oh boy, what a little slut you are. Knew you'd be responsive. Knew you were a little bitch. You big tough guys are always the slutty ones.'

Dean whimpered as Chas added a lubed finger to his hole and run it around, adding a second finger to prep Dean. They both knew even if Chas added all his fingers to Dean's hole, nothing would really ever prepare him for Chas's massive dick.

'It's okay my pretty agent. Gonna stretch you open, gonna take care of you.' Chas was sweating now and pulled off the wig. Dean had expected him to be clean shaven like Victor had been and was pleasantly surprised to see that Chas has close cropped hair. He was the most handsome man Dean had ever seen, except for Victor of course, and with the corset and makeup he was making Dean realise he had a whole new set of kinks now. And this was so not going to be a one-time thing. 'Can you take three, four?' Chas asked. Dean nodded, widening his legs as much as he could in readiness. Chas soon had four fingers inside, stroking him and making him hard again. Dean groaned and bucked his hips.

'Not yet pretty.' Chas chuckled. Dean was beginning to love that sound. 'You're gonna come on my cock.'

Chas moved back and lubed up his glorious cock. Dean's eyes widened as it grew bigger, sleeker, darker and he whimpered again.

'Fuck.' He moaned and Chas shot him a look. 'Sorry...you're just...so fucking big.'

Chas laughed. 'Okay I'll let that one go.' He climbed off the bed and returned with a set of thigh to ankle cuffs that he fitted to Dean, keeping his legs back and open. 'You're amazing too. Pretty little hole just begging for my cock.'

Dean groaned as Chas lined up and slipped his head into Dean's ring. So far so good. Dean almost relaxed, thinking that the prep had been enough, he could take this. Then Chas shoved harder and Dean screamed. It hurt, goddamn hurt so much. He was sure he had been split.

'No...don't...can't...' Dean sobbed and tried to buck away from Chas. Now he knew why Chas had used the restraints.

'It's gonna hurt my pretty agent, but then it will feel so good. I promise.' Chas said so gently, as he leaned down and stroked Dean's heaving chest, then swiped over his already hard nipples and made him squirm harder. Dean took deep breaths. He could do this. He'd been to Hell. He'd been to purgatory. He'd let Benny, a fucking vampire, fuck him. He could deal with pain. He opened his eyes and looked at Chas. He'd wanted this with Victor and now he had it. Be careful what you wish for. He actually managed a shaky smile.

Chas grinned back at him. 'Okay now tough guy?' He shoved again and Dean let himself scream, but this time he was riding the pain, taking it, relishing it. Chas was huge, he was already so full, he didn't know how anymore could possibly fit. Then Chas pulled him closer and further apart and Dean howled as Chas shoved in harder, deeper, deeper....and now the pain was being overtaken by the feeling of fullness, of being complete and he felt that he would never be empty again. As Chas moved Dean felt electric jolts course through his entire body from his prostate.

'Yeah, that's it pretty, knew you could take it, knew you'd like it. Yeah.' Chas was groaning and thrusting, so close to coming and he ran his fingertips over Dean’s nipples, then tweaked them, just as he hit Dean's prostate at just the right angle and Dean screamed, his body completely stiff as he came, his second hard orgasm of the night.

 

When he came to, he was lying in strong arms against a muscular chest. For a moment he thought he was having that dream again, the totally inappropriate one about Sam, but then he opened his eyes and saw the arm across his chest was a gorgeous deep brown colour and he smiled, looking up at Chas. Dean could feel the come leaking from his stretched out hole and a rational part of him knew he should have checked that Chas wore a condom, but he was too fucked out right now to care.

'Hey, pretty.' Chas grinned. 'Told you I'd take good care of you.'

Dean smiled back, feeling completely relaxed for the first time in months. 'You sure did.'


	2. Part Two

**Summary for the Chapter:**

> Follows on from Chastity's Bar, and Dean gets to know Chas a whole lot better........

‘You have a real fuckable mouth. Once you've had a rest you're going to suck me.' Chas smirked.

Dean felt his smile fade. 'You gotta be kidding me.'

'Uh huh. Don't tell me you haven't sucked dicks before.' Chas raised a perfectly plucked eyebrow.

'Never one as big as yours.' Dean complained. 'It was a tight fucking fit up my arse, I can't get that thing down my throat.'

Chas laughed. 'You will, Pretty. It’s not your decision. I know what's best for you.' He had removed the heels and stockings, but still wore the corset.

Dean took in the sight of him, miles of glowing dark brown skin, muscular arms and chest, beautiful face with thick full lips, a radiant smile and warm brown eyes. The make-up and corset should make Chas look ridiculous, but they just made Dean want him more.

Dean subconsciously licked his lips and Chas laughed again. 'Oh yeah, get them nice and moist for me, Pretty.'

'Chas, please, can you do something for me?' Dean asked.

'Sure.' Chas raised an eyebrow in anticipation.

'Can you say Winchester, it's been a while before you fuck me?'

Chas looked puzzled, then grinned. 'Shit. You really had a thing for my bro didn't you? So what's your real name Pretty? I guess you and Stretch ain't real feds.'

'Dean. Dean Winchester. Sam’s my brother.' Dean bit his lip and blushed. ‘Um, Victor, he was kinda after us. Caught us a couple of times. Not that we're criminals....'

'Hush. I don't need to know. I just need to get those lips around my cock.' Chas grinned. He pulled Dean up by the arm and off the bed. Dean tried to gain his footing but Chas growled 'On your knees. Over to the bench.'

Dean crawled over to a small bench covered in pink leather and leaned across it. It was the perfect height for him to suck Chas off and for Chas to take him from behind. Chas squatted down and grabbed Dean's hair, making Dean look up at him.

'Hey, Winchester. It's been a while.' Chas almost purred the words and Dean felt his cock twitch. 'Stay right where you are.' Chas released his hair and moved away, coming back in shortly to show Dean what he had in his hand. A large butt plug, pink of course. Dean stifled a laugh.

'So while you're mouth's busy I'm gonna keep your tight little hole busy too. Pink for my Pretty.' Chas moved to Dean's rear and ran the plug around Dean's hole, before lubing it up and pushing it in. Dean was still loose, but he was also still sore and he stifled a whimper as it entered him. Once it was in place, Chas came back to stand in front of Dean.

'Winchester. It's been a while.' He repeated and held out a small box, flicking a switch. Dean felt the plug start to vibrate and he groaned.

'Oh shit, fuck, no....' Dean cursed as the plug worked inside him and his cock started to harden again.

Chas was there by his face, his dick huge and ready. 'Open up, pretty little Dean-o.'

Dean wanted to tell Chas to go to hell, wanted to keep his mouth stubbornly closed, but he had to let out another groan and Chas gripped his hair again and pushed his dick inside Dean's mouth. Dean gagged and panicked at first but Chas stroked his hair and murmured encouragement to him and Dean relaxed and started to suck at the thick long flesh filling his mouth.

Dean felt Chas pushing harder and the huge dick started to fill his throat. Dean gagged again and Chas pulled out, letting him gasp for air before pushing back in again. This went on for several minutes with Chas moaning variations of ‘fuck yeah’ ‘take it bitch’ ‘that’s it’ and Dean’s choking and gagging just seemed to make Chas harder.

Dean hated the fact that being used like his, drooling and fighting for breath, was turning him on too. That and the plug relentlessy massaging his prostate of course. Dean eventually managed to swallow Chas down and Chas groaned loudly as he emptied his load down Dean's throat. Dean could no longer draw breath and the world went white, then black, as he passed out with Chas's dick still lodged inside him.

When he came to, he was back on the bed and lying in now familiar strong arms and he smiled up at Chas. Chas was naked and had removed all his make-up. He looked younger and even more handsome.

'Hey there, Deano. Sorry about that.' He purred as he stroked Dean’s chest with his fingers.

'Don't be.' Dean's voice was a harsh rasp. 'How long...'

'You've been out of it for about half an hour.'

'Shit, I should go, Sam'll...’ Dean started to panic.

'Don't worry I sent him a text from your cell.' Chas grinned. 'Just saying don't wait up.'

Dean laughed and winced at the soreness of his throat. Chas removed his arm from Dean's chest and handed him a bottle of water. Dean gulped it down. 'Thanks. But I'll have to go soon.' Dean sighed. 'Wish I could stay.'

‘You can come back here anytime you need to.’ Chas said sincerely. Dean felt his dick twitch. He liked the way Chas had said need, not want, but need. Chas understood him.

‘I think I may need to come back soon.’ Dean grinned. ‘And I'll follow you into your pink room of pain and let you do whatever the hell you want.'

Chas laughed and hugged him close. 'I look forward to that, pretty Little Dean-o.'

 

The case wrapped up too quickly. It was a standard vamp killing and Dean felt cheated. He had wanted to stay a while longer, explore that pink room….

‘Dean? Earth to Dean Winchester?’ Sam’s voice broke into his thoughts.

‘What?’ He snapped. He was almost surprised to find himself sitting in booth in a diner opposite Sam, his breakfast sitting untouched before him.

‘Where to next? And where the fuck is your head today?’ Sam snapped back.

‘I’m just tired. We were up all fucking night killing that vamp.’ Dean hissed, keeping his voice low so the other diners didn't overhear.

‘I asked if you wanted to keep the room and get some sleep.’ Sam said in that annoying voice that was almost a whine.

‘I just want to get moving.’ Dean pushed his plate away and pulled out some dollars to leave for the food. ‘You can drive, I’ll sleep in the car.’

‘Are you ill?’ Sam asked. ‘You haven’t touched your food.’

‘I’m fine. Not hungry.’ Dean stood up. All he wanted in his mouth was that thick black cock, choking him, filling him, completing him. He shook his head. Fuck, perhaps Chas was some kind of witch. Why couldn't he get him out of his head?

‘Okay.’ Sam sighed and Dean didn’t need to meet his eyes to know his brother would be frowning at him in concern. Once in the Impala Sam hesitated before starting the engine. ‘Is it the girl you spent the night with? Do you wanna say goodbye?’

‘Give me a break.’ Dean growled. ‘Fuck off. Just drive.’ He slid down in the seat and lent against the window, not wanting Sam to see how close to the truth his words had been.

It was six weeks later that they had a lead on a shape shifter a few miles from Chicago. It had been six weeks of torture for Dean. More than once Sam had caught him watching hard core gay porn on his laptop and Dean had shrugged it off with a smile and an ‘it takes all sorts Sammy.’ So now Dean wracked his brains for an excuse to go into the city, to go back to the bar. For once luck was on his side as the shifter was not only responsible for the death they had come to investigate, but possibly several in Chicago.

‘Back to the Windy City then.’ Dean grinned.

‘Didn’t know you were so fond of Chicago.’ Sam said wryly.

‘Pizza man, pizza!’ Dean said and Sam rolled his eyes.

They spent the day interviewing the victim’s friends and family, then checked into a motel not far from Chastity’s Bar. Dean was like a caged animal, roaming the small room, unable to settle.

‘Dean!’ Sam huffed in exasperation, looking up from the laptop. ‘Either watch TV, do some research or get the hell out!’

‘Sorry. Kinda restless.’ Dean gave a sheepish grin. ‘D’you wanna grab a drink?’

‘Nah, I’m onto something here. You go.’ Sam looked up, grinning. ‘Hey, you gonna find your work out partner from before? I know the signs dude.’

Dean laughed and nodded. ‘Yeah, hope to. Don’t wait up Sammy!’ Why hadn't he thought of that, just telling his brother he needed to go and get hooked up? It was partly true after all.

 

Dean felt like he was having an out of body experience as he walked into the bar. What the hell was he doing here? Chas might not even be around. He might have another ‘guest’ in his pink room. He might not be pleased to see Dean.

The bartender, the one Dean had christened Agador, recognised Dean immediately. ‘Oh hello Agent! Casual Friday is it?’

Dean was wearing jeans and a black t-shirt, nothing else. It was summer and Chicago was actually hot for once. ‘Hey. Off duty.’ Dean gave him a winning smile.

‘JD on the rocks?’ Agador asked, a twinkle in his eye.

‘You remembered!’ Dean smiled again, all the while trying not to look around the bar for Chas like a lost puppy looking for his master.

‘I always remember a pretty....everything!' Agador said as he batted his eyelashes at Dean. 'You never came back so we could thank you. You got the bastard that killed Jerry didn’t you?’

‘Yeah. Had to move on.’ Dean shrugged, sipping his drink.

‘Winchester, it’s been a while.’ A deep and sexy voice whispered in his ear from behind.

Dean’s whole body went rigid and he almost dropped his glass. ‘Fuck!’ He hissed, eyes closed, taking deep breaths.

Agador laughed and put his hand over Dean’s, settling him. ‘Looks like he found you, Agent.’

Dean was pulled round into Chas’s broad chest, arms wrapped around him in a bear hug. Then he released Dean and stood back to look at him.

‘Hey. I must of known you were coming.’ Chas teased, running his big hands up and down the tight green and gold mini-dress he’s wearing. He had green eye shadow that made his brown eyes look even richer, softer, and high heeled thigh high black patent leather boots. He towered over Dean, who could only look at him, licking his suddenly dry lips, blinking stupidly. ‘Like what you see? Green to match your eyes, Pretty.’

Dean nodded and found his voice. ‘I was on a job, here, staying nearby, had to, couldn't…’ He was talking gibberish and it didn’t matter. Chas was smiling at him and put his finger against Dean’s lips, silencing him.

‘Come with me.’ He turned and Dean followed, once more feeling like the lost puppy running after his master. Chas led him upstairs and as soon as they were in his apartment he pushed Dean up against the wall. ‘You came back. I’m surprised.’ His body was pressed against Dean’s and they were both hard already. ‘And pleased.’ He bent to kiss Dean, hard and rough, leaving Dean panting when he pulled back to look at him again.

‘I…I need…need you.’ Dean hated the need in his voice. ‘Shit! What the hell have you done to me?’

Chas raised a perfectly plucked eyebrow. ‘What do you mean?’

‘Can’t stop thinking about you. Wanting. Fuck. Never felt like this before.’ Dean moved away from the wall, over to the window, needing air. ‘You a fucking witch or something?’

Chas followed him and sat down on the large white sofa. ‘Come here.’ He patted his lap and Dean snorted out a laugh. ‘Come here, Dean.’ Chas said more insistently.

Dean sat next to the man, not touching, just looking. ‘I don’t want this. What the hell?’

‘You said it yourself, Dean. You need me. Need what I can give you. I’m not a witch but I do have superpowers. I’m the best fuck in Chicago.’ Chas winked at him.

Dean laughed despite himself. ‘You’re the best fuck I've ever had. And I’m no maiden aunt.’

Chas laughed too and pulled Dean towards him. ‘Come to Chastity, Pretty.’ Dean let himself be pulled onto the man’s lap. He put his head on Chas’s shoulder and sighed happily. ‘Good boy. Let me take care of you Dean-o.’ Chas stroked his back and hair gently, then gripped Dean’s head and moved it up to kiss him. This time it was slow, a gentle caress of tongue against lips, delving, prompting, opening, searching, until they were sucking on each other’s tongues and Dean was bucking his hips, feeling Chas’s hard dick beneath him.

‘Hey! Chastity?’ A man’s voice called out and Dean froze, shocked rigid. ‘You coming back darling?’

‘What the fuck?’ Dean scrambled off like a scalded cat and Chas laughed.

‘Shit I forgot him!’ Chas chuckled. ‘Oh Pretty don’t get jealous. He’s just a client.’ Chas stood up and adjusted his dress. ‘I never asked you to pay, remember?’ He kissed the top of Dean’s head and left Dean sitting open-mouthed on the sofa.

‘Honey I gotta let you go. Something’s come up.’ Chas turned and winked at Dean before he entered the pink room.

‘Hey I paid for an all-nighter.’ Dean heard the man grumble and the sound of chains being undone and dropped.

‘Have a full refund.’ Chas said coolly. ‘And I’ll make it extra special next week, Senator.’

‘Really?’ The man sounded excited now, not disgruntled. ‘Can I bring my collar and leash?’

‘Of course you can honey.’ Chas almost purred and Dean saw a small balding middle-aged man dressed only in ugly Y-fronts being maneuvered out by Chas. He had what looked like a suit, shirt, tie and shoes bundled up in his arms.

‘Hey, Chastity, fuck’s sake let me get dressed!’ He wailed.

Chas sighed and pushed him back into the pink room. ‘Go ahead, Be quick.’

Chas walked over to where Dean was still sitting and feeling freaked out. He squatted down and Dean could clearly see the bulge in his frilly gold panties as the dress rode up. ‘The Senator’s a fucking pervert.’ He grimaced. ‘Pays well though. Hey, Pretty, don’t freak out on me. Girl’s gotta make a living!’ He ran his hands up Dean’s thighs.

The Senator emerged from the pink room and flushed when he saw Dean. ‘You got a new boy? He’s fucking lovely.’

‘Not for you Senator.’ Chas said quickly, sensing Dean’s anger.

‘Fuck off.’ Dean growled, fists bunching. ‘I ain't for sale.’

The Senator paled and backed away to the door. ‘If you change your mind, let me know. I’m fucking filthy rich, boy!’

Chas had already moved over to the door and almost pushed the Senator out. He turned round and lent against the door with a sigh, then smiled at Dean. ‘Nasty little pervert.’ Chas smirked. ‘He’s not having you. You’re mine. Aren’t you?’

Dean felt such a mixture of anger and arousal that his head spun. ‘Fuck.’

Chas handed him a glass of JD and sat next to him. ‘So, where were we?’ He ran his fingertips along Dean’s thigh towards his groin. ‘I think I was about to give you what you need.’

‘N-uh.’ Dean stopped his hand. ‘Jesus, Chas, you literally just threw another man out!’

‘So what?’ Chas shrugged. ‘I told you. He’s a paying customer. You, on the other hand, are mine.’

‘Don’t.’ Dean shook his head. Suddenly he wanted to cry. He never cries. He’s Dean fucking Winchester. But he’s not been anyone’s for a long time. He wants to be someone’s. ‘Oh God.’

‘Dean.’ Chas stroked his face. ‘It was so good before, remember? And you needed that again, that’s why you came back. Let it go, Pretty. Let me help you.’

Dean shuddered and nodded, holding back his tears. ‘Yes.’

Chas pushed him back down on the sofa and unbuttoned his jeans, pushing them down and rubbing his already hard dick with his hand. He scooted back and lent down, taking Dean into his mouth so quickly Dean yelped in surprise and pleasure. Chas is a pro and Dean’s coming in an embarrassingly short time, screaming his release in what sounds like a fucked up prayer to God, Jesus and Chas.

Chas smiled as he moved up Dean’s body and started to kiss him. Dean could taste himself on those full lips and then when he opened up, his mouth was flooded with his own come, straight from Chas’s sinful mouth. Dean had never experienced this before and he was partly revolted but also massively turned on, especially when Chas pulled back enough to growl ‘Swallow it, Pretty.’ He swallowed hard and Chas kissed him again, until Dean was a trembling and panting mess.

Chas chuckled and climbed off, letting Dean take big lungfuls of air.

‘My turn now Pretty.’ He stood by the sofa, a vision in green and gold. ‘On your knees.’ Dean flopped straight onto his knees from the sofa and looked up at Chas. ‘Take me out, then suck me. Make it last.’ Chas ordered and Dean pushed the dress up, the tight gold panties down and started to lick the huge dick in front of him. He gripped Chas’s firm thighs and Chas had his hands on Dean’s shoulders.

‘That’s it. Take your time.’ Chas groaned and Dean wondered how long Chas can keep going, he was already rock hard and Dean could feel the tremors under the skin of his thighs.

Dean licked and nibbled and slid his tongue along the underside of the smooth hard dick and Chas groaned louder. ‘Fuck! Fuck going slow! Now, goddamit.’ He grunted and pushed inside Dean’s mouth. Dean chuckled and the vibrations seemed to make Chas even harder. ‘Fuck! Yes!’ Chas was so hard now, Dean was having trouble doing anything at all other than keep breathing. Just when he thought Chas was going to come down his throat, the man pulled out and thick spurts of come hit Dean in the face, luckily his eyes were already squeezed shut. Once again his was slightly repulsed but also aroused; no one had ever shot come all over him before. It made him feel dirty and used but in a weirdly good way. It made him feel like he was owned and that he belonged.

‘Fuck! So fucking good, Pretty!’ Chas groaned. ‘You look so fucking hot covered in my come!’

Dean knelt back, unsure what to do now. Should he wipe it off, leave it, wait for Chas to instruct him? This was all new territory. He wiped his eyes with a shaky hand and blinked up at Chas.

‘Want to cover every inch of you.’ Chas was fisting his own dick and looking at Dean hungrily. ‘Stay where you are.’

Dean nodded, feeling light headed and watched as Chas pumped his dick, amazed that the man could get hard again so quickly, then realised that he was hard again too. Dean groaned and put a hand down to touch his own dick.

‘No!’ Chas panted. ‘That’s mine!’ Dean dropped his hand and nodded his acquiescence.

Chas groans increased and he came, this time hitting Dean’s chest and it dripped down over his stomach, trailing towards his groin. Dean whimpered and writhed as his own arousal grew.

‘Fuck, yes, God.’ Chas panted. ‘So fucking beautiful.’ Chas sank to his knees and pulled Dean in to kiss him, both of them breathless and shaking. Dean was so hard now he whined in the back of his throat and Chas chuckled. ‘Want something Pretty?’

‘Need…God…need to come…please!’ Dean gasped.

‘Not yet.’ Chas ran a hand down and enclosed the base of Dean’s dick with his long, strong fingers.

‘Please!’ Dean almost sobbed.

‘Lie down.’ Chas helped Dean move from his kneeling position onto his back, still holding his orgasm at bay. ‘Take your top off.’

Dean struggled out of his t-shirt and blinked up at Chas, pleading with his eyes. ‘Look at those sweet little nipples.’ Chas grinned. ‘Gonna make you feel so good Dean.’ He started to nibble at one and ran his fingertips over the other and Dean’s body went rigid, his dick getting harder still despite Chas’s fingers holding him. Chas teased him for several minutes, alternately lapping and rubbing each nipple, but for Dean it felt like hours. Dean was grunting and whimpering, the odd word escaping, usually ‘Please’ or ‘fuck’ and then Chas started to suck his left nipple really hard and Dean’s hips bucked up as Chas released his dick. Dean screamed as his orgasm overtook him and he spurted all over his stomach, joining the mess already there from Chas.  
Chas rubbed the spunk into his stomach and over his thighs and Dean’s spent cock twitched. ‘Told you Pretty, gonna cover every inch.’ Chas murmured. ‘So beautiful.’

Dean was exhausted and just lay watching Chas, then sighed happily when Chas flopped down next to him. ‘I’ve got you pretty Dean-o.’ Chas whispered, pulling Dean into his arms. ‘God you must be special. Not only did I fuck you in my lounge but now I’ve got spunk all over my new dress. Gonna be a bitch to clean.’

‘Shoulda taken it off.’ Dean smirked.

‘Plenty of time for that later.’ Chas kissed him tenderly. They lay for a while just relaxing. Dean was almost asleep when Chas stirred. ‘I have to go back down for a while, close up and stuff.’ He sighed. ‘You can wait for me here or in the pink room.’ He raised an eyebrow. ‘Your decision. But no showering. I haven’t finished with you yet.’

Dean grinned back. ‘Pink room.’

Chas got up and pulled Dean to his feet. He led Dean through to the big pink bed. Dean’s eyes flitted around the room, looking for signs of the pervert Senator.

‘Don’t worry Pretty, he was only on the cross. Not in the bed. That’s all yours.’

Chas secured Dean spread-eagled on the bed, cuffed at each wrist and ankle. ‘Fuck look at you. Damn I wish I could stay right here!’

Dean listened to Chas showering and then he came back in, wearing a skimpy black dress. He kissed Dean and left without another word. Dean was asleep before the door closed.

 

Dean woke up to a strange sensation. His dick was hard, there was a warm, wet feeling around it….

‘Fuck!’ He hissed and his dick started to pulse inside Chas’s warm mouth. He grunted and thrust into the welcome heat, his body already wired and ready to go even if his brain is still sleepy. It didn’t take long for Dean to come and this time Chas swallowed him down, then sat up with a satisfied smile.

‘Wakey wakey!’ He grinned.

Dean was dumbstruck. Chas was now wearing a black corset, pulled in tight at the waist, low enough just to skim his nipples. He undid Dean’s ankles and lifted his legs up, pushing them back.

Dean snapped more awake. ‘Shit, Chas, give me a second!’

‘Why?’ Chas grinned, then lent down and plunged his tongue into Dean’s hole. Dean groaned and wished his hands were free so he could grab Chas’s head, shoulders, something. A finger joined the very talented tongue and Dean could barely believe that he was getting hard again. Two fingers and the tongue had Dean squirming and gasping. Chas pulled out and smiled at Dean.

‘Now I’m gonna paint your ass Pretty.’ Chas thrust into him, holding Dean’s legs back and pounding in hard and deep.

Chas pulled out with a grunt just at the point of ejaculation and the warmth of his spunk covered Dean’s ass and thighs. Dean’s dick made a valiant effort and he came too, without even being touched and Chas laughed.

‘God you’re amazing.’ He gasped and flopped down next to Dean, resting his head on Dean’s heaving chest. ‘Only need to cover your back now, Pretty.’

‘Fuck-fucking hell.’ Dean groaned. ‘You, you’re the amazing one.’

‘Why thank you Pretty!’ Chas said, smirking. He ran a fingertip over Dean’s nipples and Dean groaned.

‘No, no more. Can’t.’ He pleaded. ‘S’too much.’

Chas laughed again. ‘I’ll give you a little respite.’ He stroked Dean’s flat stomach. His skin felt itchy and stiff from the dried and not so dry come plastered over him.

‘Chas, I’ve never done this before, I mean, I like to be in control, I find it hard…’ Dean tried to express his confusion.

‘Shush. I know you Dean. I know how hard and tough you are. I know what you need. No one can be so self-contained and in control all the time. You don’t need excuses. You just need me.’ Chas started to brush over his nipples again. ‘What do you need?’

‘You. Fuck. Need you. Only you.’ Dean whimpered as Chas pinched his hard nipples.

‘Get on your hands and knees, Pretty.’ Chas said as he undid the wrist cuffs and Dean moved onto all fours as instructed. 

‘Winchester. It’s been a while.’ Chas whispered into his ear, then started to fuck him, deep and hard again before pulling out and coating Dean’s back with his come. He fisted Dean’s cock until Dean came too and he rubbed Dean’s come into his back along with his own, both of them groaning in pleasure.

‘There. All painted up, Pretty Little Dean-o.’ Chas sighed in contentment. ‘All mine. And next time I’m going to get you in a corset too.’ Dean gave a little sigh of pleasure too and nestled into strong arms.

They fell asleep in each other’s arms and woke up almost stuck together in places. Dean once again felt more relaxed and happier than he could ever remember. He selfishly hoped it would be a while before they found the shifter.

**Author's Note:**

> This is the first fic I posted and I'm a little nervous. Comments will be appreciated, cherished and even framed!
> 
> I miss Victor Hendrickson & think he should have been around a lot longer, hence this fic!


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